


Curious Jack

by spn_glow



Category: Supernatural
Genre: Anal Fingering, Anal Rimming, Anal Sex, Blow Job, Bottom Jack Kline, Curious Jack, First Time, M/M, One Shot, Top Sam Winchester
Language: English
Status: Completed
Published: 2018-11-09
Updated: 2018-11-09
Packaged: 2019-08-20 23:57:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,400
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16565606
Author URL: https://archiveofourown.org/users/spn_glow/pseuds/spn_glow
Summary: Jack is wanting to know what it’s like to touch someone and what it’s like to be touched. He wants to know how it feels. When he gets close to Sam he wants to explore his physical side with the tall, strong hunter.





	Curious Jack

Jack still has a lot to learn about himself. Being a powerful Nephilim is great now that he knows how to use his grace, the human side of him is more of a mystery than the angel side at this point.  
Humanity is complicated.  
He’s glad to have Sam and Dean to help him with things. 

Lately he has been wondering about intimacy. He sees how Dean enjoys physical time with women, how he kisses them before bringing them back to his room. He doesn’t spy on Dean but sometimes when he comes home late at night with a woman he won’t notice Jack sitting in a chair below the stairs reading, so he finds the interaction fascinating.  
Jack wants to touch, to be touched, he just isn’t sure what that means. 

One evening when Jack is getting a snack, Dean comes in looking for some grub too. Jack doesn’t have the “think before you speak” mindset and his innocence makes him see nothing wrong with saying what’s on his mind.

“Dean, does it feel good to kiss someone?” 

“Uh...you want to know about kissing?” 

“Yes, what’s it like?”

“Well...it’s awesome actually. To feel someone else’s lips with yours paves the way for more fun things” Dean said.

“More fun things?” 

Shoot, how did he get stuck being the one to have this talk with Jack? 

“Yea, there’s more than kissing but you should start with that until you know you are ready to go further” 

“Further than kissing?”

Oh man, well it looks like Jack needs the sex talk. Vague answers are not enough on this one. 

“You know what sex is don’t you Jack?”

“Yes, I know what the act is but how do you pick someone to do it with?” Jack asked with his serious look that always reminds Dean of Castiel.

“Well, you will feel a certain way about someone, want to be closer, you’ll be drawn to them”

Jack nodded as he thought about that.

“Don’t rush it kid, it’ll happen when it’s right” 

Dean gave him a pat on the arm and walked out.

Later Jack was in his room when Sam tapped on the open door.  
Jack looked up smiling at him.

“Hi Sam”

“Hey Jack, you ready to watch a movie?”

“Yes. Can we have popcorn?” 

“It’s already done and waiting for us” Sam said.

“Great! Jack said getting up to walk with Sam to his room.

Sam has a tv set up so they hang out and watch shows and movies together. They sit on the bed and Sam grabbed the bowl of popcorn sitting it down between them so they can share it. 

“What are we watching tonight?” Jack asks.

“I picked The princess bride, it’s a good one and funny, you’ll like it”

Jack smiled and leaned back against the headboard settling in.

Halfway through the movie they finished the popcorn and Sam moved the bowl to the night stand. When he re-situated himself he was shoulder to shoulder with Jack. Normally Jack wouldn’t pay attention to that but he’s very aware of his personal space lately. He liked feeling Sam next to him. When Sam laughed his shoulder was moving against his. He started to feel warm. Sam moved over slightly. Jack adjusted towards Sam to feel the connection again. Sam wasn’t paying attention and not phased. 

The movie ended and Sam looked at Jack.

“Did you like it?”

“It was great Sam”

Jack was looking at Sams face and then at his lips. Without thinking he put his hand on Sams cheek. Sams eyes shifted away then back to Jack.

“Uh..? Jack?”

Jack leaned in and was only able to brush his lips to Sams before Sams eyes widened as he fumbled at his surprise pulling away. 

“Jack what are you doing?”

“Giving you a kiss”

“I got that, but why?”

“I want to know what it’s like to kiss you” 

“Jack, I don’t...I don’t know if that’s a good idea”

“Why?”

Sam cleared his throat.

“Please be my first kiss Sam, I want it to be with you” 

Sam hesitated. He can’t deny he is feeling turned on by Jack’s interest and the thought of being Jack’s first...anything. He would never take advantage of Jack but since he brought this up himself he can make sure this is special for Jack.

“I do want to kiss you Jack”

He smiled at Sam not sure what to do next. Sam did though. He turned towards Jack looking at him with a new expression. Sam put his hands on Jack’s neck and jawline, he bit his lip as he ran a thumb over Jack’s soft lips watching them spread under his touch. Sam leaned in and pressed his lips to Jack’s. Jack kissed back, he matched Sams movements, lips pressing, closing, opening, and again. So smooth and pliant. Sam deepened the kiss sticking his tongue in Jack’s mouth searching for his, they met and massaged together. Jack loves the feel and the taste of Sam’s mouth, the light scruff feels good rubbing against his skin, and the sound of Sam breathing through his nose is arousing him further. Jack put his hands on Sams shoulders and ran them down his chest over his shirt. Sam put his arm around him and pulled Jack closer so their chests pressed against each other, Jack squeezed at Sams waist. The kissing gets heated, heavy. Sam finds the hem of Jack’s shirt and pushes his hand under it to feel his bare skin. Jacks breath hitches at the touch and Sam swallows the sound with his mouth. 

Jack leans back just for a moment and takes his shirt off. He watches Sam as his eyes look over his body. Jack wants more, wants to see Sam. Knowingly, Sam removes his shirt too, tossing it aside. Sam is toned with defined muscles, tan skin, has chest hair, so beautiful. Jack feels his pants get tighter.

They start kissing again feeling their skin touch, bump, and rub. Sam begins kissing Jack’s neck, he sucks his skin, he kisses to his ear, nibbles his ear lobe, Jack is giving quiet moans. When Sam licks over his ear and inside it he feels tingles all over his body, he digs his fingers in Sams back. 

Sam guides Jack to lay down while he keeps trailing kisses over each collarbone, down the middle of his smooth chest. He kisses to a nipple and sucks gently, Jack moans feeling the sensitivity from Sams tongue swirling over and around it making it bud instantly. Sams lips kiss across to give the same attention to his second nipple. Kissing and suckling while he rubs and gently pinches at the one he left. Jack’s breathing is getting heavier, he’s turning to mush under Sams touch. Sam continues to kiss down his middle, kissing all over, his ribs, his belly, his hips, across the skin above his belt line. Jack is fully hard now, he is very aware of his swelling. Sam kisses back up until he’s kissing those perfect lips again. He puts his hips against Jack’s pushing against him, moving their bulging hard ons together. 

“Sam you feel so good”

“Yea baby? You like me touching you?”

“Yes, so much”

“You like feeling me on top of you? Pushing against you?”

“Mhm, I need more”

“Tell me baby, tell me what you need”

“Touch me more Sam, touch me here” 

Sam watched as Jack rubbed his hand over his own dick squeezing at it through his pants.

Sam shuttered seeing Jack do that, it’s so sexy and he’s sure Jack doesn’t even know he’s being a dirty boy.

Jack grabbed at Sams ass and pushed his bulge against Sams.

“You sure Jack? 

“Yes, please Sam”

“Ask me again baby”

“Please touch me Sam, touch me more”

Sam pulls Jack’s pants and boxers down off his legs getting him fully naked. The sight is sinful, Jack has no idea how sexy he is. Sam grabs his legs under his knees and pulls him so his ass is at the edge of the bed. Sam gets on his knees in front of him.

“I want you to watch me suck you Jack” 

He leans up on his elbows so he can see Sam like he asked.

Sam runs his big hands over Jack’s thighs and spreads them wider. He wraps one hand around his shaft and he feels it pulse from the new touch. Sam licks the tip over the slit and Jack’s mouth opens with a gasping moan. Sam makes eye contact for a split second then starts giving kitten licks to the head. Jack is vocal already. Sam closes his lips around him and begins swallowing his length and dragging his tongue upward with his motion. Sam is steady as he sucks and licks long strokes. The wet heat has Jack jerking with pleasure, he grabs at the sheets trying not to buck into Sam. It feels so good inside his mouth.  
Jack’s breathing is getting rapid, Sam slows and pulls off not wanting him to come yet. 

Sam spreads his legs more and marvels at his untouched pink hole. His dick twinges from the sight. Sam rubs his thumb over the virgin hole and Jack jumps on reflex. Sam smiles biting his lip, his eyes lust blown.

“Oh Jack you look so good for me like this” Sam said with a low voice. Jack can only moan in response. 

Sam bends down and begins rimming him slowly, licking over his opening and circling around again and again with a kiss every few rotations. Sam lets out small groans in his throat from the sweet musky taste. Jack is panting heavily, throwing his head back in bliss. The sensation is intense, he tangles a hand in Sams hair and pulls a little, Sam moans sending vibrations to the sensitive skin and Jack whines. He lets go of Sams hair and pulls his legs up holding the backs of his knees to his sides so he is spreading even more for Sam. Mmm, so limber Jack is. Sam uses the extra access to start opening him up. He pushes a finger partially inside beside his licking tongue. Sam is aching with desire, he takes a free hand and undoes his belt and zipper frantically and grabs himself stroking his length for some friction. 

Sam continues to push his finger inside, feeling the tight space squeeze. He watches Jack as he adds another finger, his face is flushed and breathing uneven, Sam loves how Jack is a mess for him. 

“I want to fuck you Jack, you’ve got me so hard for you baby”  
He keeps moving his fingers inside him.

“I want to have sex Sam, I want more of you” he says breathy.

Sam stands and drops his jeans to the floor, his dick is engorged and leaking. Jack feels a wave of pleasure looking at Sam naked, his body is so wonderfully sexy. Jacks eyes take in Sams size and he starts to feel nervous. 

“Sam, is it going to hurt?”

“Are you scared?” Sam asks softly.

“A little” Jack said looking up under his lashes.

Sam crawls over Jack kissing him again and rutting against his leg gently.

“I’ll go slow baby, it will hurt at first but then it feels really good, promise” he kisses him again. 

Sam leans up and holds one of Jack’s legs up while he lines his tip to his hole, he pushes it in. Jack scrunches his brows and winces. Sam continues to push inside, the muscles protest at the intrusion and Jack’s body tenses.

When he feels the muscles accept, he pushes all the way in. Jack yells out clawing at Sams arms. He feels very stretched and pressure, so much pressure. Sams dick is bigger even after using his fingers to work him open, Jack feels himself ripping open as Sam pushes inside him.

“Sam! Ah! Oh, oh, oh!” It’s stretching me, oh... f-fuck, ah!”

“Relax baby, you need to relax, it’s okay. Damn you feel so good baby”

Sam stays still while Jack breathes heavy as his hole adjusts to him. He kisses over Jack’s neck and face. Jack meets his eyes and Sam pulls halfway out and thrusts back in, Jack moans out. Sam’s hips begin a nice slow rhythm into Jack’s tight, wet hole. Jack is holding onto Sams sides, his legs wrapped around his waist. Sam angles and hits that bundle of nerves making Jack cry out.

“Yea, that’s it, let my dick make you feel good baby. You’re taking it so good” 

Sam pounds into him again and again, Jack cries and moans out with each thrust inside him, he swears Sam is going to break him, he’s holding back his grace so he can feel the full human experience. Each thrust is painful, then it becomes different, he doesn’t get used to it but pleasure blends with it, he feels it deep in his belly. Sam is grunting as he relishes in taking his virginity, it’s all his, Jack is his. He slams that sweet spot several times in a row and Jack has no warning or control as he comes all over himself and Sam. His body trembles through his orgasm. Watching Jack get off and feeling him spill his hot creamy seed on their skin sent Sam to the edge. He pumped harder and faster until his load came spurting out, filling Jack up. Sam grunts through it and the after shocks. He is breathing in Jack’s ear. Jack nuzzles his cheek to Sams while he holds onto Sam tight. 

Sam gently pulls out and lays on his back pulling Jack to lay on his chest so he can rub his arm and run fingers through his hair. Jack drapes a leg over Sams. They lay together listening to each other taking breaths, Jack is tuned in to Sams heart beats like this. Being with Sam this way is better than anything he’s experienced, angel or human.

“Are you okay Jack?”

“I am more than okay Sam, that was....amazing”

“You are amazing” Sam kissed his temple.

“I already can’t wait for our next movie night” Jack cuddled further.

Sam smiled at that. He has so much more for Jack, so much more. This is just the beginning.

**Author's Note:**

> Please leave a kudo if you liked reading and feel free to comment :)


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